


Hell's Wings

by Wanzamaximoff



Category: Supernatural
Genre: Alternate Universe - Angels & Demons, Angel/Demon Relationship, Heaven vs Hell, M/M, Mental Health Issues, Multi, Other Additional Tags to Be Added, Other Ships Not Mentioned in Tags, Post-Traumatic Stress Disorder - PTSD, Tags Are Hard
Language: English
Status: In-Progress
Published: 2020-10-12
Updated: 2020-10-12
Packaged: 2021-03-08 01:34:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,680
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26963770
Author URL: https://archiveofourown.org/users/Wanzamaximoff/pseuds/Wanzamaximoff
Summary: The sheer quantity of living demons and angels was diminishing. Heaven and Hell had come to an agreement to cease fire so that the balance could be restored.But what the hell does that have to do with human Dean Winchester?
Relationships: Castiel/Dean Winchester, Gabriel/Sam Winchester, Lucifer/Michael (Supernatural)
Kudos: 5





	1. They call her Destiny

Dean Winchester was boring. He knew that, his brother knew that, hell, even his late girlfriend had known that. He was a boring mechanic in a boring Midwestern town with a boring future. Most of his days consisted of airing up tires for folks that didn't know how ~~or didn't want to waste their precious time~~ and filling up the wiper fluid for their windshields. After work, he'd stop by Ellen's bar and check up on her. 

“Dean.” Ellen’s curt voice cuts through the air of the empty bar and Dean’s steps falter slightly through the threshold.

“Hey, Mrs. Harvelle.” Dean’s young voice replies quietly. He sits down at the bar sheepishly and glances at the older woman. “How’re you holding up?” Ellen Harvelle’s daughter passed away two years ago and today was the anniversary. Ellen looks away to hide her emotions from the 21 year old.

“Same as always, I ‘spose.” She shoves a beer towards him. “I hear Sam’s coming into town again. When’s the last time you boys even spoke to each other?” Dean froze at the news of his brother and he takes a drink of the beer to hide his nerves.

"Not that long ago.” Dean lies through his teeth, making sure to hold eye contact with her. “Is he bringing Jess again?”

"If you’re going to lie about talking to Sammy, you should at least keep up to date,” Ellen shoots him a dirty look. “Sam and Jessica broke off their engagement about a year ago.” Dean startles at this and frowns into the abyss of his beer.

”Why’s that?” He grumbles quietly.

”They wanted different things, I guess. Bob was telling me how Jessica wanted to be a big city psychiatrist but Sammy wanted to come home. He also expressed interest in having children, something she definitely did not want.”

Dean cringes at the nickname of ‘Bob’ for his godfather, Bobby, but he nods along with the rest of what Ellen said. The reason fit what he knew about Jess, but the change of Sam’s values was a little weird. But what Sam did was none of his business, he made that perfectly clear two years ago.

_Dean hadn’t been himself for a few months after Jo had died in the car accident. Dean himself was still recovering from it: he’d been forced into a boot with a single crutch to hold onto with his left arm and his right was in a cast. He had never been this useless in his life and he **hated** it with a burning passion. He had too much time to live in his head and relive the trauma over and over and over again. He’d always known that he had some trauma that had remained untouched from his childhood but he didn’t need it to suddenly crop up alongside the accident. _

_Sam had been as patient as he could be at the time but Dean couldn’t wrap his head around that. So Dean, as all good coping methods go, lashed out at his brother and blamed him for Jo’s death; because Dean wouldn’t have gone to prom if Sam hadn’t convinced him so of course it was his fault. His little brother had never had such a hurt expression on his face and Dean wished he could say that that was where the hurt ended: it wasn’t. Dean kept blaming him and yelling at him for hours. Sam sat through it all without lashing back once._

_The next day, Sam told him that he was heading back to his university in Boston to finish his bachelor’s and that if Dean needed him, to just call._

_Dean told him to go fuck himself._

_That was the last Dean had heard from his baby brother._

Dean says his goodbyes to Ellen and he gets into his beautiful Chevy Impala. He peels out of the parking lot with rocks flying every which way. He’s on the highway heading home when his cassette tape player starts acting up. With a weary sigh, Dean fiddles with it with his right hand while keeping his left on the wheel. He has to keep flickering his eyes between the road and the music player. Dean’s been driving since he was 13, he’s confident in his multitasking abilities while behind the wheel. 

His confidence is paid back with shit luck. A semi comes flying around the corner, in his lane, and slams headfirst into his beautiful car.

”Dean Winchester is dead.” Whispers a soft voice from the shadows, blue eyes twinkling with regret. 

**Notes for the Chapter:**

> Hey all!  
> I haven't written anything in a long, long time! I got inspired by one of those romance phone games and decided to pick it up again. As I haven't written in forever, please forgive any errors you find!


	2. Is this purgatory, God?

Dean was never a religious guy. He knew when he did wrong and when he was supposed to ask for forgiveness (not that he did.) But in this very moment? Dean wishes he had been religious. If he was, it would explain what he was currently seeing.

In front of his eyes is a world so twisted that he thinks David Bowie is going to pop up with leggings so tight that even Dean questions his sexuality. Dean stands on a single lone boulder while a pond floats upside down above his head without shedding a single drop. To his right is a twisted creature advancing on an oblivious infant with wings; to his left is his brother, his Sammy, sitting at a long dinner table filled to the brim with Dean's favorite foods, beckoning him ever closer. In front of Dean sits a bar with the sign behind it saying 'Winchester Brewery' and a beautiful brunette with the prettiest blue eyes ever in front of it.

Dean's scared to take the risk, but he glances behind him to see if that holds a path. What he sees behind him makes his breath catch and his eyes start to water.

She sits there in his car with the biggest smile he's ever seen. It's the first time Dean's ever seen her wear a dress or makeup. Her hair is done up with curls that bounces when she laughs- ~~curls that lain flat caked in blood.~~

"Jo..." Dean's voice cracks and he drops to his knees, his back to his girlfriend. This can't be real. Jo's dead. Sam hates him. This is all a bad dream. She's dead. She's dead. She's dead. _I'm dead_ , Dean realizes suddenly. He pulls his hands away from his face and freezes at the sight of blood on them. "What the hell..."

"You have to make a choice, Dean." A voice, not feminine nor masculine, whispers in the wind. "Otherwise you will be stuck here..."

"Where is _here?!_ " Dean yells and he jumps to his feet. "Where the hell am I?!" His eyes scan his surroundings with unadultered panic. He can't be dead. He never got to tell Sam he was sorry. He never got to meet Charlie's girlfriend. He never got to read Garth's completed novel. He was only 21.

He was only 21. _She was only 18._

"Choose." The voice ignores the question and Dean realizes that's all he was gonna get from it. _Was that God?_ Dean asks himself, bitterly. If so, they were a right prick.

A shrill infant cry breaks Dean's self loathing and his eyes shoot to his right. The creature from earlier, a twisted morph between a wolf and a human, has its wolfish mouth latched onto the wing of the baby human. Dean freezes momentarily, wishing for a moment that he was prepared to handle such monsters on the fly, before he remembers his other surroundings. Dean lurches forward off of his floating boulder and his stomach slams into the wooden bar. He groans softly and his eyes look up to see the beautiful brunette looking at him with slight disappointment in her eyes but a gentle smile on her lips. 

"Welcome to Winchester Brewery, Dean. I hope you enjoy your stay. You can call me," the woman hesitates as if to come up with her name on the spot, "Cassiel. I'm your bartender." 

Dean blinks in surprise at the woman knowing his name but he shakes his head.

"No, this is all wrong." He straightens up and he grabs the glass bottle he had jumped for. "What the hell kinda name is Cassiel?" Dean grins at the girl and he slams the glass bottle against the edge of the bar, shattering half of the bottle. "Sounds like a pornstar." He mumbles without looking at her. He turns back towards the boulder and swears when he notices it's starting to float away. He takes a deep breath.

"I'm dead anyways. Fuck it." He runs towards the boulder as fast he can, knowing that he'd have to jump the growing gap. Dean swears he feels a gust of wind pushing him forward but he can't think much of it as he takes the leap of faith. Dean does the dumb thing and he glances down as he jumps; he sees the nothingness of blue sky and pink clouds for miles upon miles.

Dean clears the boulder easily and he lands on his knees with a grunt. Pain shoots up his legs and he gasps as flashbacks attack him. The flashbacks remind him that he was so, so close to being paralyzed for the rest of his life but he didn't care. He had been angry over what had been done to him instead of being grateful for what he still had. Panic builds in his chest and his reckless resolve to save the winged infant starts to fade. 

"You're safe. Keep going." The voice comes again and it brings along a blanket of calm. Dean shudders at the sudden loss of pain and memories but he's thankful. He sends a thanks to whatever god is controlling this purgatory. He struggles to his feet but he manages it. The broken bottle sits undamaged and he grabs it. He turns to his left and he glares at the monstrosity. 

"There's no need to be an asshole to a baby, _asshole!_ " Dean growls. He takes a step back before he runs and jumps once again.

Except this time his feet never find purchase.


End file.
